


To Kill or Not to Kill

by orphan_account



Category: Supernatural
Genre: Assassin!AU, M/M, Minor Castiel/Dean Winchester
Language: English
Status: Completed
Published: 2013-07-07
Updated: 2013-07-07
Packaged: 2017-12-17 14:50:57
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 2,869
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/868784
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>Gang leader, Crowley, hires the Winchesters to take out two key members of his rival gang. When Sam unknowingly meets one of the targets at a bar, he agrees to a date.</p>
            </blockquote>





	1. Part 1

Sam sat on the cheap motel bed with a sigh; he had arrived in Broward County, Florida a little over an hour ago and was already itching to leave. He hadn’t even wanted to take this job, but Crowley insisted that he and Dean were the only ones who could pull it off.

Crowley was the leader of a notorious street gang, Hell’s Demons, and was often hiring the Winchesters to take care of his dirty work. The Demons were a ruthless gang that had spread throughout the country. They were in a constant fight for control against their rival gang, The Fallen Angels.

Sam snorted at the ridiculous cliché the entire situation created: Angels against Demons. Originally dean and him had made most of their profit by staying unattached and taking the jobs that paid more, taking out a few from each gang regularly. It was perfectly balanced until Sam started dating the Demon’s third in command, Ruby. That had been a toxic relationship from the start; she got him addicted to hard drugs and got him to start the biggest war between the gangs yet. He had the great pleasure of ganking her ass in the end.

Crowley had taken over soon after and was leading the efforts to wipe out the Angels. Dean hated working for him, claiming he was cheating them out of fair pay for their hits, but there wasn’t much they could do about it. The ‘King of Hell,’ as he liked to call himself, made it clear that if they didn’t do as they were told, there would be grave consequences.

So they had been sent to Florida with the promise of their freedom after this job. They hadn’t been given any information on the hit except that the two targets were crucial to the Angel’s plans. They had hopped into Dean’s ’67 Chevy Impala and made the long drive down.

“Are you just going to mope around until Crowley calls?” Dean interrupted his thoughts.

Sam rolled his eyes at his brother, “What else am I supposed to do?” Irritation coated is words, “Crowley didn’t give us any information and if they recognize us before we even know who they are, they’ll skip town or kill us!”

“Relax,” Dean put his hand on Sam’s shoulder, “they won’t recognize us. The only Angel we ever dealt with directly was Michael and he’s dead.”

“I know.” He grumbled.

“Then go out to a bar and drink,” Dean gestured toward the door, “you’re depressing me.”

“You just want me out so you can watch porn.” He stood up and headed for the door anyway.

“Shut up.”

* * *

 

Sam slouched on the bar stool, avoiding eye contact with anyone. He’d learned from a young age to be inconspicuous when in public. His dad had raised Dean and him into this life, never taking no for an answer. They knew how to shoot straight by the time they were twelve and had made their first kill before graduating high school. Sam was reluctant and never enjoyed killing like his dad did and ran away countless times. He was always brought back by Dean, who, despite doing everything Dad asked, really did want the best for him. Dean even helped get him the money to go to Stanford. He was brought back into the business by the sudden disappearance of his dad. They never found him.

“Serves him right, tyrannical bastard.” Sam mumbled under his breath.

“You tell ‘em, Sasquatch.” Sam jumped at the unexpected voice.

 The man next to him had to be nearly a foot shorter than him. He stared at Sam with a mischievous glint in his amber eyes. He was wearing an expensive looking leather jacket and jeans.

“Are you done checking me out, Moose?” The man grinned.

Sam straightened, “Stop that.”

“Stop what?”

“Calling me names.”

The mystery man bent over the bar laughing, “We’re not in kindergarten anymore, Gigantor,” he paused to catch his breath, “but if it really bothers you, you could always tell me your name.”

“Campbell,” Sam lied smoothly, “Sam Campbell.”

“Gabe.” The other man, Gabe, signaled for another drink, “I’m guessing by your luscious locks that that’s short for Samantha.” He winked.

Sam rolled his eyes, “Are you always this annoying?”

“Yes,” the bartender came over with a chocolate martini, “endearing isn’t it?”

Sam scoffed in response, but couldn’t help feeling that Gabe was right. He relaxed a little and sipped his drink.

Gabe turned, completely facing Sam, “So, what’s your story?” he poked Sam in the side, “I come in here all the time and I definitely would’ve noticed a pretty moose like you.”

“Don’t call me a moose.” Sam glanced over at Gabe.

“Aw,” Gabe pouted, “but it’s such an accurate description.” He sipped his drink, “You didn’t answer my question.”

“Me and my brother are travelling across the country,” he shrugged, “we’re just passing through.”

“That’s a shame,” Gabe seemed to visibly deflate, “I’d love to take you to dinner.”

Sam shrugged, “We’ll be here for a couple days,” he stood up, realizing that Dean would be looking for him soon, “We could get dinner before I leave.”

The smaller man beamed, “Here’s my number,” He grabbed Sam’s hand and scribbled his phone number on him, “text me.”

Sam smiled, “I will.” He turned and walked out, an unfamiliar happiness spreading through him.

* * *

Sam walked into the motel room still grinning like an idiot. Dean was lying in his bed, still fully clothed, humming ACDC.

“Hey, dude.” Sam swept passed his brother and sat on his own bed.

“Why are you so happy?” Dean sat up to stare at his usually sulky brother.

Sam glanced over at him, “I think I have a date.”

The older Winchester leaned toward his brother excitedly. Ever since Ruby, Sam had been reluctant to do any sort of dating. “Is she hot?”

Sam hesitated, Dean didn’t know that Sam wasn’t _exclusively_ into girls and he wasn’t sure how he would take the news. Their father would have torn him a new one if he had found out.

“Yeah,” he decided that now wasn’t the right time to discuss his sexuality with Dean, “she’s pretty hot.”

“Awesome, man,” He high fived his brother, “I’m glad you’re getting back in the game.”

  Soon Dean turned out the light and curled up under the covers. Sam pulled his phone out of his pocket and put in Gabe’s number. He sent a quick text to the other man, hoping he was still awake.

**Hey, it’s Sam from the bar –S**

He set his phone on the nightstand, not really expecting a reply. He was just drifting off to sleep when he heard his phone buzz. He picked it up and read the message.

**Hello, Moose, I didn’t think I’d ever hear from you! Lunch tomorrow at noon? I know a great Italian place. –G**

Sam chuckled and quickly typed his response.

**Thought you wanted to take me to dinner? –S**

**Can’t wait that long. Is that a yes? –G**

**Yes. Where do you want to meet? –S**

**I’ll pick you up. See you then, Samsquatch. ;) –G**

Sam threw his phone back onto the nightstand. He was glad that Gabe had bumped up their date to lunch, he couldn’t wait either. Sam marveled at the butterflies in his stomach, it had been years since a date had made him this giddy and nervous. He hadn’t felt this way since he’d dated Jess. He couldn’t believe a man he’d just met could make him feel this way. Love at first sight was bull shit, but he still couldn’t ignore the flips his stomach did whenever he thought of Gabe. He closed his eyes, knowing exactly who would be making an appearance in his dreams tonight.


	2. Part 2

Sam woke up to Dean singing ‘Heat of the Moment’ too loudly. He groaned and rolled over, pulling the covers up over his head. He felt a pillow hit him and Dean’s muffled voice, “Come on, man, it’s 11:45, are you _ever_ getting up?”

Sam bolted upright, “It’s WHAT?!” Sam scrambled out of bed, running to the bathroom, “Shit. Shit. Shit.”

Dean stared curiously after him, “What?”

“My date will be here in fifteen minutes, Dean!” he called as he ran a brush through his hair, “Can you get me some clothes?”

A second later Dean knocked on the door. Sam opened it, toothbrush dangling from his mouth, and grabbed the jeans and plaid shirt his brother handed him. He got dressed as quickly as possible, hoping Gabe wouldn’t decide to show up early. As soon as he walked out of the bathroom, still buttoning up his shirt, he heard a car honk outside.

“Shit, that’s him.” he grabbed his phone and wallet and hurried out the door.

He heard Dean’s voice behind him as the door swung shut, “HIM?”

Sam cursed his carelessness, knowing he would have to have that talk with Dean when he got back. He sighed and looked around; next to the Impala was a brand new red Mustang.

His jaw dropped open when a familiar head stuck out of the driver side window. “You coming, Moosey?”

Sam hopped into the expensive looking car and buckled up.

Gabe started talking immediately, “So, there’s this awesome Italian restaurant, Il Toscano, just down the street. I was thinking we could go there for lunch then grab some ice-cream before I brought you back.”

“That sounds awesome.” Gabe backed out, “You didn’t tell me you had money.”

“That would be a little rude, don’t ya think?” He glanced over at Sam, “’Hello, I’m rich, wanna go out to dinner?’”

“Point taken.” Sam turned to look at the other man, “So, what do you do that you can afford cars like this?”

Gabe glanced at him uncomfortably, “It’s kind of a family business. I’m not overly fond of the work, me and my little brother have been trying to quite for some time.”

Sam nodded, “I know how that feels, Dad raised me and Dean into the life. I tried to go to Stanford Law, but we had a family crisis and I had to come back.”

“Would you leave again?”

“I don’t think I can,” He laughed bitterly, “Dean doesn’t like being alone, even though he would never admit that.”

“Your dad?”

“Dead,” Sam said calmly, “presumably.”

They sat in silence for the rest of the ride. When they finally arrived at the restaurant, Gabe walked around the car and opened Sam’s door.

“After you, Princess.”

Sam didn’t dignify him with a response, instead walking past him and into the restaurant. It was a nice place with beautiful décor.

Gabe came up behind him, “Let’s go out to the patio, it’s a lot quieter out there.”

Sam nodded and followed him out. They sat in the corner away from the rest of the crowd. The waiter came and took their order and they sat in a comfortable silence.

After ten minutes Gabe couldn’t stand it anymore, “So, you went to Stanford,” he broke the silence, “there must have been some hot nerdy girls there, right?”

Sam smiled, “Just one,” his heart clenched at the thought, “her name was Jess.”

“What happened?” Gabe could tell that it hadn’t ended well.

“Drive by shooting,” his voice cracked a little, “she was dead before the paramedics arrived.”

Gabe reached across the table and grabbed Sam’s hand, “I’m sorry.”

Sam shrugged, “It happened six years ago.”

Gabe stared at Sam, “You loved her.”

“Yes.”

He sat back in his chair, and nodded. He opened his mouth to speak as Sam’s phone started ringing.

The taller man pulled out his phone and ignored the call, Dean could wait.

“Aren’t you going to answer?” Gabe questioned

Sam shook his head, “Probably not important.”

A look crossed Gabe’s face, but was gone before Sam could identify it. He could feel his phone buzzing with new messages in his pocket. A second later, the waiter brought out the food. Sam took advantage of Gabe’s momentary distraction to check his phone.

**Dude, answer your god damned phone! –D**

**Crowley sent us the details of the targets. –D**

**You better not be dead! –D**

**It’s Castiel and Gabriel Novak, Michael’s little brothers. I’ll send you the pictures. –D**

The first picture was a dark haired man in a trench coat, his neck was covered in tattoos and he held a machete in his hand. The second picture looked a lot less threatening, and very familiar. The amber eyes and golden brown hair were immediately recognizable.

“Gabriel…” Sam stared at his date with a panicked expression.

Gabe looked up from his food, “Yeah?”

Sam jumped out of his seat, “We need to go.” He started walking away; turning to see the other man was still sitting with a shell shocked expression. “NOW!”

Gabriel jumped out of his seat and followed Sam out to the parking lot.

“You need to get your brother and run.” Sam started pacing, wondering why he didn’t just pull a gun out and shoot Gabe. “Don’t ask questions; just get as far away from here as you can. Get new I.D.s and-“

His sentence was cut off by a familiar click of a gun behind him. He turned and saw Gabe pointing a handgun at him.

“Slow down there, Winchester,” He grinned, “no need to tire yourself out.”

“You knew?”

“Of course,” Gabe laughed, “Do you think Michael didn’t give us proper warning about the WINCHESTERS?” He took a step forward.

Sam winced, “So this was all just a ploy to get me alone.” He laughed bitterly, “You just wanted to kill me.” He didn’t understand why that simple fact hurt him so much, he hadn’t even known this man for 24 hours.

“Don’t be stupid, Moose,” Gabriel took another step toward Sam, he was within arm’s reach now, “I was going to kill you on your way home from the bar. I don’t play with Cas’ safety.”

“Well, why didn’t you?” Sam growled.

Gabriel closed the space between them, pressing the gun into Sam’s abdomen, “I thought you were interesting, fun. I had hoped I could convince you to leave, appeal to your kindness. I bet Michael never thought of that.”  

Sam looked down at the other man coldly, “Who says I’m kind?”

Gabe burst into laughter, “When you found out who your target was, you panicked and told me to run. You don’t want to kill me,” Gabe grinned, “and I don’t want to kill you. Come with me, Sam, you can go to Stanford and become a lawyer just like you’ve always wanted.”

He had to admit that the idea was tempting, “Dean-“

“Is dead.”

Sam felt a cold dread spread through him, “He’s what?”

“I sent Castiel to take care of him after I picked you up.”

Something inside Sam broke. Dean had been his only family, the only person he could rely on, and now he could be dead. It was all is fault for trusting Gabe.

“Take me back.”

“No,” Gabe shook his head, pressing the gun harder into him, “you’re either going to leave town, or I’m going to shoot you.”

Sam didn’t stop to think, he reached down and kissed Gabriel. He half expected the gun to go off, but instead Gabe dropped it and pulled Sam closer. When they broke apart, Sam pulled his infamous puppy eyes and whispered, “Take me to my brother, please.”

Gabe hung his head in defeat, “Get in, Samsquatch.” they both climbed into the car and sped away.

After a few minutes of silence Gabriel spoke, “What are you going to do?”

Sam looked at him curiously.

“Your brother is dead.” He glanced at Sam suspiciously, “Are you going to come after me and Cas?”

Sam took a deep breath, “If dean is dead,” he stated calmly, “you’re going to have to shoot me.”

Gabriel nodded, not sure if he could actually kill the younger Winchester. A large part of him hoped he wouldn’t have to.

They reached the motel in record time and Sam jumped out before the car had even stopped moving. He ran to the room, throwing the door open, expecting the worst. The first thing he noticed was the sound of his brother breathing heavily. Next he saw the figure in a trench coat straddling Dean.

“DEAN!” Sam’s first instinct was panic, but that was squashed when he heard his brother moan.

Dean looked over to his brother guiltily, “I’ve been thinking, Sammy, Crowley’s a dick, we need a new alliance.” The dark haired man, Castiel, looked over at Sam, a similar look of guilt on his face. “Also, I might be a bit gay.”

Sam sighed with relief as Gabe walked up behind him. “See?” He said nonchalantly, “Nothing to worry about.”

Sam spun around and grabbed Gabe in a desperate kiss. “I love you.”

Gabriel smirked, “I know, Samsquatch.”

Sam know that they would all need to go into hiding for a while, Crowley was not the kind of person you could screw over with no consequences, but, in that moment, Sam didn’t care. As long as he had Gabe, everything would be alright. 


End file.
